EP0570159A1 - Rubber compositions for curing-bonding, method of cure-bonding and metal-rubber bonded articles - Google Patents

Rubber compositions for curing-bonding, method of cure-bonding and metal-rubber bonded articles Download PDF

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Publication number
EP0570159A1
EP0570159A1 EP93303529A EP93303529A EP0570159A1 EP 0570159 A1 EP0570159 A1 EP 0570159A1 EP 93303529 A EP93303529 A EP 93303529A EP 93303529 A EP93303529 A EP 93303529A EP 0570159 A1 EP0570159 A1 EP 0570159A1
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EP
European Patent Office
Prior art keywords
rubbers
rubber
metal
bonding
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP93303529A
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German (de)
French (fr)
Inventor
Keisaku Yamamoto
Kiyoshi Ikeda
Junichi Koshiba
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Publication date
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Publication of EP0570159A1 publication Critical patent/EP0570159A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2321/00—Characterised by the use of unspecified rubbers

Definitions

  • the present invention relates to rubber compositions for cure-bonding, a method of cure-bonding and metal-rubber bonded articles. More particularly, the present inventicn relates to a technique of bonding a metal and a rubber which can be applied to a wide variety of combinations of metals and rubbers without using adhesives and can provide a very large bonding strength with keeping the mechanical properties of rubbers at a high level.
  • non-polar rubbers having a low unsaturation degree represented by ethylene-propylene rubber (EPM) and ethylene-propylene-nonconjugated diene rubber (EPDM) are inferior in adhesion to metals.
  • EPM ethylene-propylene rubber
  • EPDM ethylene-propylene-nonconjugated diene rubber
  • the task to be attained by the present invention is to provide a technique of bonding metals and rubbers which can be applied to a wide variety of combinations of rubbers and metals including non-polar rubbers having an unsaturation degree, need no adhesives and can provide a very large bonding strength with keeping the mechanical properties of rubbers at a high level.
  • the inventors have conducted intensive research in an attempt to attain the above task and have accomplished the present invention.
  • one of the present inventions relates to a rubber composition for cure-bonding of metals which comprises a rubber component and at least one metal acrylate compound represented by the following formula (1): (wherein R represents a hydrogen atom or a methyl group, M represents a mono- to tri-valent metal atom, m represents an integer of 1 to 3 and n represents an integer of 0 to 2).
  • Another invention relates to a method for cure-bonding a metal and a rubber by curing the above rubber composition in contact with the metal.
  • Still another invention relates to a metal-rubber bonded article obtained by curing the above rubber composition in contact with the metal.
  • the rubber component in the present invention is unlimited and a wide variety of rubbers can be used.
  • the rubbers are natural rubbers, isoprene rubbers, butadiene rubbers, styrene-butadiene rubbers, chloroprene rubbers, nitrile rubbers, butyl rubbers, ethylene- ⁇ -olefin copolymer rubbers or ethylene- ⁇ -olefin-nonconjugated diene copolymer rubbers (including ethylenepropylene rubber and ethylene-propylene-nonconjugated diene rubber), chlorosulfonated polyethylene rubbers, acrylic rubbers, epichlorohydrin rubbers, silicone rubbers, fluororubbers and mixtures thereof.
  • nonpolar rubbers having a low unsaturation degree such as ethylene- ⁇ -olefin copolymer rubbers and ethylene- ⁇ -olefin-nonconjugated diene copolymer rubbers which have been considered not to be able to provide sufficient adhesion according to the conventional methods can be used.
  • the metals used in the present invention are unlimited and various metals can be used. Examples are magnesium, calcium, barium, titanium, zirconium, iron, cobalt, beryllium, aluminum, chromium, manganese, nickel, copper, zinc, tin, cadmium, silver, platinum, gold and lead.
  • the metal acrylate compounds used in the present invention are those which are represented by the formula (I) mentioned above.
  • M represents a mono- to tri-valent metal atom.
  • the metal atom are lithium, sodium, potassium, magnesium, calcium, strontium, barium, manganese, iron, cobalt, nickel, copper, silver, zinc and aluminum.
  • the metal acrylate compounds are zinc acrylate, magnesium acrylate, aluminum hydroxyacrylate, zinc methacrylate, magnesium methacrylate and aluminum hydroxymethacrylate.
  • the metal acrylate compounds may be used each alone or in combination of two or more.
  • the ratio of the rubber component and the metal acrylate compound is preferably 0.1-50 parts by weight of the metal acrylate compound per 100 parts by weight of the rubber component.
  • amount of the metal acrylate compound is too small, the bonding strength obtained is sometimes insufficient.
  • it is too large the effect of increasing the bonding strength to be obtained by increasing the amount is saturated and this is uneconomical and besides, the mechanical properties of the rubber are sometimes deteriorated.
  • the rubber composition of the present invention is bonded to metals by so-called cure-bonding method which comprises curing the rubber composition in contact with metals.
  • cure-bonding method which comprises curing the rubber composition in contact with metals.
  • the curing agent is not critical and, for example, organic peroxides and sulfur can be used.
  • the rubber component and the metal acrylate compound of the present invention and optionally carbon black, organic peroxide, antioxidant, curing accelerator, processing aid, stearic acid, reinforcing agent, filler, plasticizer, softening agent and the like are mixed by ordinary kneaders such as rolls and Banbury mixer to obtain a curable rubber composition.
  • Curing is generally carried out at a temperature of 120°C or higher, preferably 150-220°C for about 1-30 minutes. Any of press curing, steam curing and hot-air curing can be applied.
  • metal-rubber bonded articles where the metal and the rubber are bonded at a large bonding strength can be obtained.
  • These articles include, for example, various electrical equipments and rubber vibration insulators for automobiles.
  • the present invention can be applied to various combinations of metal and rubbers. Since adhesives are not needed, there is no fear that the metal and the rubber to be bonded are stained with adhesives. Furthermore, the rubbers bonded by the present invention maintain the mechanical properties at high levels. The bonding strength realized by the present invention is markedly large with retaining these features.
  • the present invention is illustrated by the following examples and comparative examples.
  • Example 1 in Table 1 The components shown in the column of Example 1 in Table 1 (excluding the peroxide) were kneaded by a 1500 cc Banbury mixer adjusted to 90°C at a rotor velocity of 60 rpm for 5 minutes. Then, the mixture was kneaded with a peroxide by an open roll mill of 8 inches to obtain a rubber composition. Then, the rubber composition was allowed to contact with an iron sheet (SS41) and subjected to press curing (170°C x 15 minutes) at this state to carry out cure-bonding of the iron sheet and the rubber. Sticking of the rubber to the surface of the press was inhibited by putting a Teflon sheet between the surface of the press and the rubber composition. Evaluation of the properties was conducted in accordance with JIS K6301 unless otherwise especially notified.
  • Example 1 was repeated except that the metal acrylate compound was not used. The conditions and the results are shown in Table 1.
  • the present invention provides the technique for bonding metals and rubbers which can be applied to various combination of metals and rubbers including non-polar rubbers and according to which very large bonding strength can be obtained without using adhesives with maintaining the mechanical characteristics of rubbers at high levels.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Rubber compositions for cure-bonding to metals comprise a rubber component and at least one metal acrylate compound of formula (I):
Figure imga0001
wherein R is hydrogen or methyl, M is a mono-, di- or tri- valent metal atom, m is 1, 2, or 3 and n is 0, 1 or 2 and may be bonded to the metal without using adhesives by curing in contact with metal.

Description

  • The present invention relates to rubber compositions for cure-bonding, a method of cure-bonding and metal-rubber bonded articles. More particularly, the present inventicn relates to a technique of bonding a metal and a rubber which can be applied to a wide variety of combinations of metals and rubbers without using adhesives and can provide a very large bonding strength with keeping the mechanical properties of rubbers at a high level.
  • It has been known that non-polar rubbers having a low unsaturation degree represented by ethylene-propylene rubber (EPM) and ethylene-propylene-nonconjugated diene rubber (EPDM) are inferior in adhesion to metals.
  • Under the circumstances, the task to be attained by the present invention is to provide a technique of bonding metals and rubbers which can be applied to a wide variety of combinations of rubbers and metals including non-polar rubbers having an unsaturation degree, need no adhesives and can provide a very large bonding strength with keeping the mechanical properties of rubbers at a high level.
  • The inventors have conducted intensive research in an attempt to attain the above task and have accomplished the present invention.
  • That is, one of the present inventions relates to a rubber composition for cure-bonding of metals which comprises a rubber component and at least one metal acrylate compound represented by the following formula (1):
    Figure imgb0001
    (wherein R represents a hydrogen atom or a methyl group, M represents a mono- to tri-valent metal atom, m represents an integer of 1 to 3 and n represents an integer of 0 to 2).
  • Another invention relates to a method for cure-bonding a metal and a rubber by curing the above rubber composition in contact with the metal.
  • Still another invention relates to a metal-rubber bonded article obtained by curing the above rubber composition in contact with the metal.
  • The rubber component in the present invention is unlimited and a wide variety of rubbers can be used. Examples of the rubbers are natural rubbers, isoprene rubbers, butadiene rubbers, styrene-butadiene rubbers, chloroprene rubbers, nitrile rubbers, butyl rubbers, ethylene-α-olefin copolymer rubbers or ethylene-α-olefin-nonconjugated diene copolymer rubbers (including ethylenepropylene rubber and ethylene-propylene-nonconjugated diene rubber), chlorosulfonated polyethylene rubbers, acrylic rubbers, epichlorohydrin rubbers, silicone rubbers, fluororubbers and mixtures thereof. One of the great merits of the present invention is that nonpolar rubbers having a low unsaturation degree such as ethylene-α-olefin copolymer rubbers and ethylene-α-olefin-nonconjugated diene copolymer rubbers which have been considered not to be able to provide sufficient adhesion according to the conventional methods can be used.
  • The metals used in the present invention are unlimited and various metals can be used. Examples are magnesium, calcium, barium, titanium, zirconium, iron, cobalt, beryllium, aluminum, chromium, manganese, nickel, copper, zinc, tin, cadmium, silver, platinum, gold and lead.
  • The metal acrylate compounds used in the present invention are those which are represented by the formula (I) mentioned above. In the formula, M represents a mono- to tri-valent metal atom. Examples of the metal atom are lithium, sodium, potassium, magnesium, calcium, strontium, barium, manganese, iron, cobalt, nickel, copper, silver, zinc and aluminum. Examples of the metal acrylate compounds are zinc acrylate, magnesium acrylate, aluminum hydroxyacrylate, zinc methacrylate, magnesium methacrylate and aluminum hydroxymethacrylate. The metal acrylate compounds may be used each alone or in combination of two or more.
  • The ratio of the rubber component and the metal acrylate compound is preferably 0.1-50 parts by weight of the metal acrylate compound per 100 parts by weight of the rubber component. When amount of the metal acrylate compound is too small, the bonding strength obtained is sometimes insufficient. When it is too large, the effect of increasing the bonding strength to be obtained by increasing the amount is saturated and this is uneconomical and besides, the mechanical properties of the rubber are sometimes deteriorated.
  • The rubber composition of the present invention is bonded to metals by so-called cure-bonding method which comprises curing the rubber composition in contact with metals. When the rubber component per se has no curing sites, it is necessary to use a suitable curing agent. The curing agent is not critical and, for example, organic peroxides and sulfur can be used.
  • For curing, the rubber component and the metal acrylate compound of the present invention and optionally carbon black, organic peroxide, antioxidant, curing accelerator, processing aid, stearic acid, reinforcing agent, filler, plasticizer, softening agent and the like are mixed by ordinary kneaders such as rolls and Banbury mixer to obtain a curable rubber composition. Curing is generally carried out at a temperature of 120°C or higher, preferably 150-220°C for about 1-30 minutes. Any of press curing, steam curing and hot-air curing can be applied.
  • Thus, metal-rubber bonded articles where the metal and the rubber are bonded at a large bonding strength can be obtained. These articles include, for example, various electrical equipments and rubber vibration insulators for automobiles.
  • The present invention can be applied to various combinations of metal and rubbers. Since adhesives are not needed, there is no fear that the metal and the rubber to be bonded are stained with adhesives. Furthermore, the rubbers bonded by the present invention maintain the mechanical properties at high levels. The bonding strength realized by the present invention is markedly large with retaining these features.
  • The present invention is illustrated by the following examples and comparative examples.
    • Example 1
  • The components shown in the column of Example 1 in Table 1 (excluding the peroxide) were kneaded by a 1500 cc Banbury mixer adjusted to 90°C at a rotor velocity of 60 rpm for 5 minutes. Then, the mixture was kneaded with a peroxide by an open roll mill of 8 inches to obtain a rubber composition. Then, the rubber composition was allowed to contact with an iron sheet (SS41) and subjected to press curing (170°C x 15 minutes) at this state to carry out cure-bonding of the iron sheet and the rubber. Sticking of the rubber to the surface of the press was inhibited by putting a Teflon sheet between the surface of the press and the rubber composition. Evaluation of the properties was conducted in accordance with JIS K6301 unless otherwise especially notified.
  • Results of the evaluation are shown in Table 1.
    • Comparative Example 1
  • Example 1 was repeated except that the metal acrylate compound was not used. The conditions and the results are shown in Table 1.
    • Comparative Reference Example 1
  • Using the rubber composition of Comparative Example 1 which contained no metal acrylate compound, bonding of the rubber to a metal was carried out with a commercially available adhesive. That is, Chemlock 205 (trademark for an adhesive manufactured by Rhode Far East Incorporated) was coated on an iron sheet and air-dried for one day. Thereon was further coated Chemlock 238 (trademark for an adhesive manufactured by Rhode Far East Incorporated) and air-dried for one day. Thereafter, the rubber composition brought into close contact with the adhesive-coated side of the iron sheet under pressure was press cured (170°C x 15 minutes). The conditions and the results of evaluation are shown in Table 1.
  • The following can be seen from the results.
  • All of the Examples accoridng to the present invention resulted in satisfactory results.
  • On the other hand, no bonding strength was obtained in Comparative Example 1 where the metal acrylate compound of the present invention was not used. Moreover, the bonding strength obtained in Comparative Reference Example 1 where the metal acrylate compound of the present invention was not used and the conventional adhesives were used was smaller than that obtained in Example 1.
    Figure imgb0002
    Figure imgb0003
  • As explained above, the present invention provides the technique for bonding metals and rubbers which can be applied to various combination of metals and rubbers including non-polar rubbers and according to which very large bonding strength can be obtained without using adhesives with maintaining the mechanical characteristics of rubbers at high levels.

Claims (10)

  1. A rubber composition for cure-bonding to metals which composition comprises a rubber component and at least one metal acrylate compound of formula (I):
    Figure imgb0004
     wherein R is a hydrogen or methyl, M is a mono-, di- or tri-valent metal atom, m is an integer of 1, 2 or 3 and n is 0 or an integer of 1 or 2.
  2. A composition according to claim 1 wherein the rubber component is selected from natural rubbers, isoprene rubbers, butadiene rubbers, styrenebutadiene rubbers, chloroprene rubbers, nitrile rubbers, butyl rubbers, ethylene α-olefin copolymer rubbers and ethylene-α-olefin-nonconjugated diene copolymer rubbers.
  3. A composition according to claim 2 wherein the rubber composition is selected from ethylenepropylene rubbers, ethylene-propylene-nonconjugated diene rubbers, chlorosulfonated polyethylene rubbers, acrylic rubbers, epichlorohydrin rubbers, silicone rubbers and fluororubbers.
  4. A composition according to claim 3 wherein the rubber component is an ethylene-α-olefin copolymer rubber or an ethylene-α-olefin-nonconjugated diene copolymer rubber.
  5. A composition according to any one of claims 1 to 4 wherein M in formula (I) is lithium, sodium, potassium, magnesium, calcium, strontium, barium, manganese, iron, cobalt, nickel, copper, silver, zinc or aluminum.
  6. A composition according to any one of claims 1 to 5 wherein the compound of formula (I) is zinc acrylate, magnesium acrylate, aluminum hydroxyacrylate, zinc methacrylate, magnesium methacrylate or aluminum hydroxymethacrylate.
  7. A composition according to any one of claims 1 to 6 comprising 0.1 to 50 parts by weight, based on 100 parts by weight of the rubber components of the compound of formula (I).
  8. A process for cure-bonding metal and rubber which comprises curing a rubber composition according to any one of claims 1 to 7 in contact with a metal.
  9. A metal-rubber bonded article obtainable by curing the rubber composition of claim 1 in contact with the metal.
  10. A process according to claim 8 or an article according to claim 9 wherein the metal is selected from magnesium, calcium, barium, titanium, zirconium, iron, cobalt, beryllium, aluminium, chromium, manganese, nickel, copper, zinc, tin, cadmium, silver, platinum, gold and lead.
EP93303529A 1992-05-13 1993-05-07 Rubber compositions for curing-bonding, method of cure-bonding and metal-rubber bonded articles Withdrawn EP0570159A1 (en)

Applications Claiming Priority (2)

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JP120429/92 1992-05-13
JP4120429A JPH05311008A (en) 1992-05-13 1992-05-13 Rubber composition for adhesion by vulcanization, method for adhesion by vulcanization, and bonded metal-rubber article

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EP0570159A1 true EP0570159A1 (en) 1993-11-18

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JP (1) JPH05311008A (en)
KR (1) KR930023413A (en)
CA (1) CA2095791A1 (en)
TW (1) TW232021B (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995012634A1 (en) * 1993-11-01 1995-05-11 E.I. Du Pont De Nemours And Company Thermally-stable melt processible fluoropolymer compositions and process
WO1997022662A1 (en) * 1995-12-15 1997-06-26 Contitech Antriebssysteme Gmbh Drive belt
EP0976784A1 (en) * 1998-02-19 2000-02-02 Japan Energy Corporation Metal/rubber adhesion promoter and rubber composition
US6809138B2 (en) 1998-02-19 2004-10-26 Nikko Materials Co., Ltd. Adhesion accelerator for bonding rubber to metal and rubber composition
EP2082900A1 (en) 2007-12-31 2009-07-29 Bridgestone Corporation Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
EP2552979A1 (en) * 2010-03-29 2013-02-06 Greene, Tweed Of Delaware, Inc. Fluoroelastomer compositions having self-bonding characteristics and methods of making same
US8389609B2 (en) 2009-07-01 2013-03-05 Bridgestone Corporation Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US20130202838A1 (en) * 2012-02-03 2013-08-08 Greene, Tweed Of Delaware, Inc. Rapid Gas Decompression-Resistant Fluoroelastomer Compositions and Molded Articles
US8546464B2 (en) 2008-06-26 2013-10-01 Bridgestone Corporation Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions
US8802755B2 (en) 2011-01-18 2014-08-12 Bridgestone Corporation Rubber compositions including metal phosphate esters
US9670341B2 (en) 2012-11-02 2017-06-06 Bridgestone Corporation Rubber compositions comprising metal carboxylates and processes for making the same
US9803060B2 (en) 2009-09-10 2017-10-31 Bridgestone Corporation Compositions and method for making hollow nanoparticles from metal soaps
CN107540884A (en) * 2017-07-19 2018-01-05 宁波拓普集团股份有限公司 A kind of adhering method of rubber and metallic framework

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KR100437321B1 (en) * 2001-06-04 2004-06-25 한국타이어 주식회사 Rubber Composition for Coating Steel Cord Having Improved Modulus
US20120100379A1 (en) * 2010-10-20 2012-04-26 Greene, Tweed Of Delaware, Inc. Fluoroelastomer bonding compositions suitable for high-temperature applications
WO2018212180A1 (en) 2017-05-19 2018-11-22 住友化学株式会社 Rubber composition for direct vulcanization bonding and molded metal/rubber composite
JP7089961B2 (en) * 2018-06-26 2022-06-23 株式会社日本触媒 Manufacturing method of molded body

Citations (1)

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WO1990008170A1 (en) * 1989-01-17 1990-07-26 Uniroyal Chemical Company, Inc. Metal acrylates as rubber-to-metal adhesion promoters

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
WO1990008170A1 (en) * 1989-01-17 1990-07-26 Uniroyal Chemical Company, Inc. Metal acrylates as rubber-to-metal adhesion promoters

Non-Patent Citations (2)

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Title
CHEMICAL ABSTRACTS, vol. 84, no. 16, 1975, Columbus, Ohio, US; abstract no. 106874n, Y.SAKURAMOTO ET AL. 'Vulcanisation and simultaneous adhesion of rubber to metals' *
DATABASE WPI Section Ch, Week 901, Derwent Publications Ltd., London, GB; Class A, AN 90-004108 & JP-A-1 287 154 (KAWAGUCHI CHEM IND KK) 17 November 1989 *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995012634A1 (en) * 1993-11-01 1995-05-11 E.I. Du Pont De Nemours And Company Thermally-stable melt processible fluoropolymer compositions and process
WO1997022662A1 (en) * 1995-12-15 1997-06-26 Contitech Antriebssysteme Gmbh Drive belt
EP0976784A1 (en) * 1998-02-19 2000-02-02 Japan Energy Corporation Metal/rubber adhesion promoter and rubber composition
EP0976784A4 (en) * 1998-02-19 2001-01-03 Japan Energy Corp Metal/rubber adhesion promoter and rubber composition
US6809138B2 (en) 1998-02-19 2004-10-26 Nikko Materials Co., Ltd. Adhesion accelerator for bonding rubber to metal and rubber composition
US20100004368A1 (en) * 2007-12-31 2010-01-07 Xiaorong Wang Metal Soaps Incorporated In Rubber Compositions And Method For Incorporating Such Soaps in Rubber Compositions
US9637613B2 (en) 2007-12-31 2017-05-02 Bridgestone Corporation Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
EP2082900A1 (en) 2007-12-31 2009-07-29 Bridgestone Corporation Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US9090127B2 (en) * 2007-12-31 2015-07-28 Bridgestone Corporation Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US8546464B2 (en) 2008-06-26 2013-10-01 Bridgestone Corporation Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions
US8901217B2 (en) 2009-07-01 2014-12-02 Bridgestone Corporation Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US8389609B2 (en) 2009-07-01 2013-03-05 Bridgestone Corporation Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US9803060B2 (en) 2009-09-10 2017-10-31 Bridgestone Corporation Compositions and method for making hollow nanoparticles from metal soaps
EP2552979A4 (en) * 2010-03-29 2013-09-04 Greene Tweed Inc Fluoroelastomer compositions having self-bonding characteristics and methods of making same
EP2552979A1 (en) * 2010-03-29 2013-02-06 Greene, Tweed Of Delaware, Inc. Fluoroelastomer compositions having self-bonding characteristics and methods of making same
US8802755B2 (en) 2011-01-18 2014-08-12 Bridgestone Corporation Rubber compositions including metal phosphate esters
US9453123B2 (en) 2012-02-03 2016-09-27 Greene, Tweed Technologies, Inc. Rapid gas decompression-resistant fluoroelastomer compositions and molded articles
US20130202838A1 (en) * 2012-02-03 2013-08-08 Greene, Tweed Of Delaware, Inc. Rapid Gas Decompression-Resistant Fluoroelastomer Compositions and Molded Articles
US10011690B2 (en) 2012-02-03 2018-07-03 Greene, Tweed Technologies, Inc. Rapid gas decompression-resistant fluoroelastomer compositions and molded articles
US9670341B2 (en) 2012-11-02 2017-06-06 Bridgestone Corporation Rubber compositions comprising metal carboxylates and processes for making the same
CN107540884A (en) * 2017-07-19 2018-01-05 宁波拓普集团股份有限公司 A kind of adhering method of rubber and metallic framework

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CA2095791A1 (en) 1993-11-14
TW232021B (en) 1994-10-11
JPH05311008A (en) 1993-11-22
KR930023413A (en) 1993-12-18

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